Ianthesine E, a new bromotyrosine-derived metabolite from the Great Barrier Reef sponge Pseudoceratina sp.
The new compound ianthesine E (1) was isolated from the Great Barrier Reef marine sponge Pseudoceratina sp. along with the known metabolites 11-hydroxyaerothionin (2), aerothionin (3) and 11,19-dideoxyfistularin 3 (4). Structures were determined on the basis of their spectroscopic data. The compounds were tested for inhibition of [(3)H] DPCPX binding to adenosine A(1) receptors in a whole cell binding assay. At 100 microM, aerothionin was the most potent, inhibiting 67% of binding, followed by ianthesine E and 11-hydroxyaerothionin which inhibited 61% of binding, and 11,19-dideoxyfistularin which initiated 51% of binding Ianthesine E (EC(50) 60 microM), aerothionin (EC(50) 42 microM) and 11,19-dideoxyfistularin-3 (EC(50) 2.6 microM) exhibited moderate cytotoxicity against the HeLa cell line.
Kalaitzis
John A
JA
Eskitis Institute, Brisbane, Qld, 4111, Australia.
Leone
Priscila de Almeida
Pde A
Hooper
John N A
JN
Quinn
Ronald J
RJ
D000818:Animals; D016466:CHO Cells; D002851:Chromatography, High Pressure Liquid; D006224:Cricetinae; D003412:Cricetulus; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D011161:Porifera / Q000737:chemistry* / Q000378:metabolism; D043682:Receptor, Adenosine A1 / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000378:metabolism
D043682:Receptor, Adenosine A1; C475724:bromotyrosine; D014443:Tyrosine